General Information of Drug (ID: DM1S5CB)

Drug Name
2-methyl-5-HT
Synonyms 2-methyl-5-hydroxytryptamine; 2-Me-5-HT; 2-methylserotonin
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 190.24
Topological Polar Surface Area (xlogp) 1.4
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C11H14N2O
IUPAC Name
3-(2-aminoethyl)-2-methyl-1H-indol-5-ol
Canonical SMILES
CC1=C(C2=C(N1)C=CC(=C2)O)CCN
InChI
InChI=1S/C11H14N2O/c1-7-9(4-5-12)10-6-8(14)2-3-11(10)13-7/h2-3,6,13-14H,4-5,12H2,1H3
InChIKey
WYWNEDARFVJQSG-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
1574
ChEBI ID
CHEBI:31085
CAS Number
78263-90-8
TTD ID
D00CRA

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
5-HT 1B receptor (HTR1B) TTK8CXU 5HT1B_HUMAN Agonist [1]
5-HT 1D receptor (HTR1D) TT6MSOK 5HT1D_HUMAN Agonist [2]
5-HT 1E receptor (HTR1E) TTCPG9S 5HT1E_HUMAN Agonist [3]
5-HT 1F receptor (HTR1F) TT0MI3F 5HT1F_HUMAN Agonist [3]
5-HT 2B receptor (HTR2B) TT0K1SC 5HT2B_HUMAN Agonist [4]
5-HT 3A receptor (HTR3A) TTPC4TU 5HT3A_HUMAN Agonist [5]
5-HT 3B receptor (HTR3B) TTR6K75 5HT3B_HUMAN Agonist [6]
5-HT 6 receptor (HTR6) TTJS8PY 5HT6R_HUMAN Agonist [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
5-HT 6 receptor (HTR6) DTT HTR6 6.43E-01 0.04 0.12
5-HT 6 receptor (HTR6) DTT HTR6 3.59E-02 -0.05 -0.48
5-HT 2B receptor (HTR2B) DTT HTR2B 1.29E-01 -0.04 -0.14
5-HT 2B receptor (HTR2B) DTT HTR2B 1.13E-01 -0.04 -0.26
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta. Proc Natl Acad Sci U S A. 1992 Apr 15;89(8):3630-4.
2 Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan. Mol Pharmacol. 1996 Dec;50(6):1567-80.
3 Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase. Proc Natl Acad Sci U S A. 1993 Jan 15;90(2):408-12.
4 Pharmacological characteristics of the newly cloned rat 5-hydroxytryptamine2F receptor. Mol Pharmacol. 1993 Mar;43(3):419-26.
5 Pharmacological profile of YM-31636, a novel 5-HT3 receptor agonist, in vitro. Eur J Pharmacol. 2000 Dec 8;409(2):195-201.
6 The 5-HT3B subunit is a major determinant of serotonin-receptor function. Nature. 1999 Jan 28;397(6717):359-63.
7 Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells. Neuropharmacology. 1997 Apr-May;36(4-5):713-20.
8 Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors. J Neurochem. 1996 Nov;67(5):2096-103.
9 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
10 Triptans in pregnancy. Ther Drug Monit. 2008 Feb;30(1):5-9.
11 Clinical pipeline report, company report or official report of Jazz Pharmaceuticals.
12 Company report (NeurAxon)
13 5-HT1B and other related serotonergic proteins are altered in APPswe mutation. Neurosci Lett. 2015 May 6;594:137-43.
14 Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor. Mol Pharmacol. 1991 Aug;40(2):143-8.
15 Irritable bowel syndrome: new agents targeting serotonin receptor subtypes. Drugs. 2001;61(3):317-32.
16 An introduction to migraine: from ancient treatment to functional pharmacology and antimigraine therapy. Proc West Pharmacol Soc. 2002;45:199-210.
17 Efficacy and tolerability of subcutaneous almotriptan for the treatment of acute migraine: a randomized, double-blind, parallel-group, dose-finding study. Clin Ther. 2001 Nov;23(11):1867-75.
18 Clinical pipeline report, company report or official report of Neurim Pharmaceuticals.
19 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
20 Lu AE58054, a 5-HT6 antagonist, reverses cognitive impairment induced by subchronic phencyclidine in a novel object recognition test in rats. Int J Neuropsychopharmacol. 2010 Sep;13(8):1021-33.
21 5-HT6 receptors and Alzheimer's disease. Alzheimers Res Ther. 2013; 5(2): 15.
22 Latrepirdine, a potential novel treatment for Alzheimer's disease and Huntington's chorea. Curr Opin Investig Drugs. 2010 January; 11(1): 80-91.
23 Therapeutic strategies for Parkinson disease: beyond dopaminergic drugs. Nat Rev Drug Discov. 2018 Nov;17(11):804-822.
24 The Serotonin-6 Receptor as a Novel Therapeutic Target. Exp Neurobiol. 2011 December; 20(4): 159-168.
25 PF-05212377 Alzheimer's Disease (Phase 2). Pfizer.
26 Activation of 5-HT6 receptors modulates sleep-wake activity and hippocampal theta oscillation. ACS Chem Neurosci. 2013 Jan 16;4(1):191-9.
27 Novel and Potent 5-Piperazinyl Methyl-N1-aryl Sulfonyl Indole Derivatives as 5-HT6 Receptor Ligands. ACS Med Chem Lett. 2010 October 14; 1(7): 340-344.
28 Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. Naunyn Schmiedebergs Arch Pharmacol. 2004 Aug;370(2):114-23.
29 Some properties of 5-hydroxytryptamine receptors in the hindquarters of the rat. Br J Pharmacol. 1979 Sep;67(1):79-85.
30 Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19.
31 New Insights into the Mechanism of Action of Viloxazine: Serotonin and Norepinephrine Modulating Properties. J Exp Pharmacol. 2020 Aug 25;12:285-300.
32 Prediction of Efficacy of Vabicaserin, a 5-HT2C Agonist, for the Treatment of Schizophrenia Using a Quantitative Systems Pharmacology Model.CPT Pharmacometrics Syst Pharmacol.2014 Apr 23;3:e111.
33 Emerging treatments for pulmonary arterial hypertension. Expert Opin Emerg Drugs. 2006 Nov;11(4):609-19.
34 Novel serotonin receptor 2 (5-HT2R) agonists and antagonists: a patent review (2004-2014).Expert Opin Ther Pat. 2016;26(1):89-106.
35 Zatosetron, a potent, selective, and long-acting 5HT3 receptor antagonist: synthesis and structure-activity relationships. J Med Chem. 1992 Jan 24;35(2):310-9.
36 Novel potent and selective central 5-HT3 receptor ligands provided with different intrinsic efficacy. 2. Molecular basis of the intrinsic efficacy ... J Med Chem. 1999 May 6;42(9):1556-75.
37 Novel and highly potent 5-HT3 receptor agonists based on a pyrroloquinoxaline structure. J Med Chem. 1997 Oct 24;40(22):3670-8.
38 Ginkgolide B and bilobalide block the pore of the 5-HT eceptor at a location that overlaps the picrotoxin binding site. Neuropharmacology. 2011 Feb-Mar;60(2-3):488-95.
39 Synthesis and structure-affinity relationships of novel N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)pyridine-3-carboxamides with potent serotoni... J Med Chem. 2003 Feb 27;46(5):702-15.
40 Co-expression of the 5-HT(3B) subunit with the 5-HT(3A) receptor reduces alcohol sensitivity. Brain Res Mol Brain Res. 2005 Dec 14;142(2):146-50.
41 Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors. Neuropharmacology. 2001 Aug;41(2):282-4.
42 Palonosetron plus dexamethasone versus granisetron plus dexamethasone for prevention of nausea and vomiting during chemotherapy: a double-blind, do... Lancet Oncol. 2009 Feb;10(2):115-24.
43 Efficacy of 5-HT3 antagonists and 5-HT4 agonists in irritable bowel syndrome: systematic review and meta-analysis. Am J Gastroenterol. 2009 Jul;104(7):1831-43; quiz 1844.
44 Emerging therapies for fibromyalgia. Expert Opin Emerg Drugs. 2008 Mar;13(1):53-62.
45 Management of postoperative nausea and vomiting: focus on palonosetron. Ther Clin Risk Manag. 2009 Feb;5(1):21-34.
46 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
47 Local anesthetics have different mechanisms and sites of action at recombinant 5-HT3 receptors. Reg Anesth Pain Med. 2007 Nov-Dec;32(6):462-70.
48 Cilansetron: a new serotonergic agent for the irritable bowel syndrome with diarrhoea.Expert Opin Investig Drugs.2005 Feb;14(2):185-93.
49 mu-Opioid/5-HT4 dual pharmacologically active agents-efforts towards an effective opioid analgesic with less GI and respiratory side effects (Part I). Bioorg Med Chem Lett. 2009 Oct 1;19(19):5679-83.
50 Cloning and characterization of the guinea pig 5-HT1F receptor subtype: a comparison of the pharmacological profile to the human species homolog. Neuropharmacology. 1997 Apr-May;36(4-5):569-76.
51 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
52 Selective seratonin 1F (5-HT(1F)) receptor agonist LY334370 for acute migraine: a randomised controlled trial. Lancet. 2001 Oct 13;358(9289):1230-4.
53 SB-216641 and BRL-15572--compounds to pharmacologically discriminate h5-HT1B and h5-HT1D receptors. Naunyn Schmiedebergs Arch Pharmacol. 1997 Sep;356(3):312-20.
54 Discovery of 5-arylsulfonamido-3-(pyrrolidin-2-ylmethyl)-1H-indole derivatives as potent, selective 5-HT6 receptor agonists and antagonists. J Med Chem. 2005 Jan 27;48(2):353-6.
55 Isolation of a mouse "5HT1E-like" serotonin receptor expressed predominantly in hippocampus. J Biol Chem. 1992 Oct 5;267(28):19761-4.
56 Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor. Eur J Pharmacol. 2004 Jan 26;484(2-3):127-39.
57 2-Substituted tryptamines: agents with selectivity for 5-HT(6) serotonin receptors. J Med Chem. 2000 Mar 9;43(5):1011-8.
58 Risperidone compared with new and reference antipsychotic drugs: in vitro and in vivo receptor binding. Psychopharmacology (Berl). 1996 Mar;124(1-2):57-73.
59 Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype. Proc Natl Acad Sci U S A. 1992 Jun 15;89(12):5517-21.